Ask TSJ: How Should I Approach This Woman I’m Sitting Next To?

askmainLife is hard. It seems like every new day brings a new question that, try as you might, you’re just unable to find an answer for. The Smoking Jacket understands this, and we’re here to help.

Each week, media sensation Tracy Pendergast and TSJ’s managing editor, Adam Tod Brown, set aside some time in their busy schedules to answer your questions in a feature we’ve cleverly named “Ask TSJ.”

This week’s question comes from Matt, a reader in Nevada…

I am out and about often, and end up seeing so many beautiful women. I don’t have the guts to go up and say hi, though. Like right now I’m in a coffee shop. A table over is a stunningly beautiful brunette with a great smile. I should go chat with her, but don’t know how to approach her or what to say!

tracyTracy Pendergast: Hey Matt! Regardless of whether she’s interested in you or not, it is always flattering for a woman to be approached. That being said, there are certain ways to go about it.

First of all, there are some places where women just want to be left alone. If you’re in a place like a coffee shop and she looks like she’s concentrating on work, I’d probably say, just let her be. Headphones are another big indication that someone doesn’t want to talk. If she doesn’t seem distracted by anything, then my best advice is a really subtle initiation. If she seems receptive and continues the conversation, keep chatting, but if she gets short with you or just smiles as a response, excuse yourself. The best way to avoid feeling awkward is knowing when to walk away!

I always think a simple joke or comment totally unrelated to her is the best way to break the ice. Then if she doesn’t seem interested in talking to you, you haven’t even put anything out there. You just seem like a friendly, outgoing guy.

If you’re trying to meet new women and don’t want to deal with the horror of approaching people you’re not sure are even single, try hanging out at places that are typically for single people. I don’t know where you live, but in New York there is a great website called and it is basically listings of all the networking events and parties going on for singles. That seems like a slam dunk to me! Then you won’t have to think up funny one-liners about heavy cream and artificial sweeteners! Good luck!!

adamAdam Brown: Well that’s a question for the ages. There are all sorts of schools of thought on the tricky subject of talking to women. Some people swear by employing a wing man. That Dos Equis guy swears that’s unnecessary though, and I tend to believe him because I’m a friendless shut-in so I prefer to believe that having a friend along for anything is pointless.

Those pickup artist types would suggest using put downs and emotional terrorism to pull a woman. I don’t doubt that it works, but being an asshole takes a special kind of dedication that not all of us have.

So, I’m afraid I’m going to have to tell you to stick with that old “just be yourself” line. It’s the only strategy that’s going to work for you. That, and you need to understand that it’s a numbers game. Don’t just talk to the women who give you an overwhelming boner, talk to every damn woman you see. Just get comfortable talking to women, no matter how attractive they are. It will help build your confidence. Women like confidence.

What should you talk about? Anything. Everything. Look for openings. If she mentions something you have a vague interest in, use that to your advantage. Keep the conversation going. You’re bound to click with someone eventually. I believe in you!

Adam Tod Brown is the managing editor of The Smoking Jacket. He would like to be your friend on Facebook and on Twitter @realadambrown.

Tracy Pendergast is a writer, model, singer, television personality and professional magician’s assistant. We might be lying about one of those facts. Check out her official website or follow her on Facebook to find out which one.

Got a question for Adam and Tracy? Click here and fire away. If we use it…your life will immediately improve for the better.